The person asking the question might actually be a tax office employee, fishing to see if anyone lets something slip as part of researching tax-avoidance methods.
For example, if you offered it as a 2×2 dinner date with a business partner’s company president, you might be able to write it off as entertainment expenses.
If you went on dates as part of a plan to run your own dating club in the future, you might be able to record them as research expenses.
Another option—which gets a bit complicated—would be to slightly overpay a business partner, and in return have them pay the offer fee as entertainment expenses on their end. That might work if the two company presidents are genuinely close.
Having acquaintances overseas opens up even more possibilities, since the Japanese tax authorities have no investigative jurisdiction there.
The reason I can casually write all this is that I never claim any of my club-related spending as business expenses. I bet quite a few small-business owners are reading this answer thinking, “Don’t mention that—whatever you do, don’t mention that method!” lol
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